How much unbottled water need pass beneath the bridge before the stain of federal prison is washed clean?

And is that just the beginning of what we might learn from Jacob Sherman’s experience?

On two spring nights, six weeks apart, in 2001, Sherman and several Earth Liberation Frontbuddies put gasoline and torch to trucks belonging to Ross Island Sand & Gravel and an Eagle Creek logging contractor. Whether he was mesmerized by old growth or Tre Arrow, Sherman spent 32 months in prison for those crimes.

On a June afternoon in 2012, Sherman received a master's degree in Educational Leadership and Policy from Portland State, and addressed his fellow graduates at the Rose Garden.

The message he carried to the podium is tattooed on his right forearm — “Dare to Fail” — and on his stomach.

A William Carlos Williams line: “No defeat is made up entirely of defeat, since the world it opens is always a place formerly unsuspected.”

At 30, Sherman is — says Michele Toppe, PSU’s dean of students — “a remarkable young man,” and one who has capitalized on “the teachable moment.”

At 19, he didn’t have a clue, much less a daily bathing ritual.

After Sherman returned from torching Ray Schoppert’s logging trucks, it was his father, Tim, who reported his suspicions about the arsons to the FBI.

In February 2003, U.S. District Judge James Redden — who ordered lawyers not to bring the word “terrorism” into his courtroom — sentenced the arsonist to 41 months in prison.

“I never tried to defend myself,” Sherman says now. “I was more interested in getting through it. I knew I deserved it. That’s the reason I pled guilty.”

He was a little naive about his just deserts. When he mentioned rehabilitation to his pre-trial detention officer, he says she leaned across her desk and said, “We don’t send people to prison to rehabilitate them. We send them there to punish them.”

But at a low-security prison outside Bakersfield, then the federal prison camp at Sheridan, Sherman found more Walden Pond than Devil’s Island. His first cellmate — Gerald Jackson, an African American in his mid-30s — led him through the maze of racial politics. (“We still talk to this day,” Sherman says.)

He read voraciously, regrouped, and reflected on the advantages he had because he was white, privileged and educated. When he was finally released to a halfway house in September 2006, Sherman had a job busing tables at the Iron Horse Restaurant in Westmoreland and a new class schedule before his first meeting with a case officer.

Five years later, Sherman is married to a middle-school teacher he met at Iron Horse. He was named the state university system’s student employee of the year in 2011 for his commitment to the peer mentor program. He earned his degree while working as many as three different jobs.

“He has used his personal experience, and his missteps, to teach his peers,” Toppe said. “They don’t have to experience what he’s experienced to learn what he’s learned.”

And Sherman organized the “Take Back the Tap” campaign, in which filtered water refilling stations on campus curb the demand for bottled water. Since 2009, he told his fellow graduates, the Smith Memorial station has eliminated the need for 125,000 plastic bottles. PSU is looking into eliminating that plastic waste stream altogether.

That prison stint, Sherman knows, didn’t disappear with the tide: “You wear a scarlet letter for the rest of your life.” But this one is now sparking conversations instead of ending them.

It’s the reason he rolls up his sleeve. The abject defeat that convinced him he is better than his mistakes.

“If we care about human suffering, there’s a lot of work to be done,” Sherman said. What sustains him is discovering it’s the daring, not the failing, that proves addictive.